A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine
Publication type: Journal Article
Publication date: 2003-05-05
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient synthesis of (6R,7R,8S,8aS)-6,7,8-trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-trihydroxyindolizidine is described from readily available N-BOC-L-proline, (BOC = tert-butoxycarbonyl) which involves the addition of ethyl lithiopropiolate to the aldehyde derived from N-BOC-L-proline as a key step, then cyclization to construct indolizidine skeletons and asymmetric dihydroxylation. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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Zhang H. et al. A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine // European Journal of Organic Chemistry. 2003. Vol. 2003. No. 10. pp. 1918-1922.
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Zhang H., Ni Y. K., ZHAO G., Ding Yu. A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine // European Journal of Organic Chemistry. 2003. Vol. 2003. No. 10. pp. 1918-1922.
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TY - JOUR
DO - 10.1002/ejoc.200200412
UR - https://doi.org/10.1002/ejoc.200200412
TI - A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine
T2 - European Journal of Organic Chemistry
AU - Zhang, HongLu
AU - Ni, Yi Ke
AU - ZHAO, Gang
AU - Ding, Yu
PY - 2003
DA - 2003/05/05
PB - Wiley
SP - 1918-1922
IS - 10
VL - 2003
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2003_Zhang,
author = {HongLu Zhang and Yi Ke Ni and Gang ZHAO and Yu Ding},
title = {A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine},
journal = {European Journal of Organic Chemistry},
year = {2003},
volume = {2003},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/ejoc.200200412},
number = {10},
pages = {1918--1922},
doi = {10.1002/ejoc.200200412}
}
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Zhang, HongLu, et al. “A Convenient Synthesis of 1-Deoxy-8a-epi-Castanospermine Diastereoisomers (6R,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine.” European Journal of Organic Chemistry, vol. 2003, no. 10, May. 2003, pp. 1918-1922. https://doi.org/10.1002/ejoc.200200412.